Brian Regan is known for his across-the-aisle brand of humor. The rubber-faced man-boy who gravitates to sweeping, accessible topics has been called “the funniest stand-up alive” by Vanity Fair and “your favorite comedian’s favorite comedian” by Entertainment Weekly.

But the highly kinetic Regan’s act isn’t static—in fact, he’s evolving, with smart political observations and opinions that can be seen on his new Netflix special, Nunchucks and Flamethrowers. Regan still aims to make 100 percent of his audience laugh, but expect a more mature comedian to grace the stage these days.

Three decades of touring up to 100 cities a year is what is called in the comedy business “a grind.” But for Regan, being on the road is what he always dreamed of. Starting off in Florida in the early 1980s, Regan worked his act out on stage up to seven nights a week. And it was the vision of traveling to make people laugh that was foremost in his mind. “It took a while before I played on the West Coast,” says Regan. “I was limited geographically. I literally bought Greyhound bus passes where you could go anywhere you want for 30 days. It wasn’t until after I moved to New York in 1986 that I began branching out and playing the West Coast states.”

It took a decade on the East Coast circuit and a chance gig with Jerry Seinfeld to open Regan’s eyes to the beauty of playing theaters, rather than clubs. “I love the complete focus you get from a theater. When you go back to a comedy club, it’s people eating nachos and there’s a blender going off in the background and the people over here, they came from New York and it’s Jack’s birthday,” Regan reflects. “It’s a different vibe, I enjoy it, but I don’t enjoy it as much as everyone sitting in velvet chairs and paying 100 percent attention.”

Even with an audience giving a comic 100 percent of their undivided attention, there is something that Regan misses from the early comedy club days, and that’s hanging out with other comedians after a gig. Which is why after a Mountain Winery show earlier this year, Regan popped by Rooster T. Feathers in Sunnyvale, just to hang out and say hello. Because for Regan, comedy clubs are his home away from home.

“That’s a great way to put it. I miss the camaraderie of comedy clubs. What’s weird at a theater is that you say good night and the audience goes and walks out one door, and you walk out another door,” he says. “Aren’t we supposed to cuddle when we’re done?”

Over the years, Regan has been adamant that he was not a comic looking to move toward a TV show or some lame sitcom about his life. Call it kismet, but the stars lined up, and Regan is now on a Farrelly Brothers-directed show called Loudermilk on the somewhat obscure AT&T Audience Network channel. “I love the autonomy of being a stand-up comedian and all the choices that come with that,” Regan admits. “Besides the amount of time I get to perform, it’s all up to me and I get to do whatever I want to do.” But when asked about the differences, it seems Regan is no longer against being on the tube. “Acting is a whole other animal. I’m thrilled that I get to do it because it’s a big deal for me. You only get this one life—might as well take on some challenges. I like the team aspect of acting. It’s real interesting to see how a TV show is made.”

For season two, Regan is being directed by either Peter or Bobby Farrelly in various episodes. “Both of them are great,” he says. “Both of them are very cool about letting me branch out and do what I want to do, but if it goes beyond what’s going to help the scene they have to reign me in. And I don’t mind because I’m serving somebody else’s creative vision. I like the difference, and I like being able to do both.”